Perfume oils containing 2-methyl-3-(3&#39;, 4&#39;-methylenedioxyphenyl)-propanal



United States Patent 4,3 3 V 3 Claims. (Cl. 167-94) This is a division of application No. 789,795, filed January 29, 195 9, new Patent No. 3,008,968.

We have discovered that 2-methyl-3- (3',4-methylenedioxyphenyl)-propanal of structure I is an outstanding olfactory ingredient in perfume-containing compositions:

It shows an exceptional tenacity. A strip of filter paper was moistened with 2-methyl-3- (3',4'-methylenedioxyphenyl)-propanal to which 10/00 of a normal anti-oxidant, e.g. hydroquinone, had been added and kept for two months in contact with air at room temperature. After this period the odor was still strong and undegenerated.

It hasan excellent stability in pure form and in perfume compositions as well as in articles in which such compositions are used, such as soaps, cosmetics, powders and aerosol products. Although 2-methy1-3-(3',4'-methylenedioxyphenyl)-propanal has a very strong, interesting and definite odor, it is easy to blend into specific and widely varying types of perfumes in relatively large amounts. This is clearly demonstrated by the examples given below.

2-methyl-3-(3,4'-methylenedi0xyphenyl) -propanal has not been described in the literature. Its lower homologue, piperonyl-ethanal or 3-( 3,4-methylenedioxyphenyl) -propanal (II) is far less interesting. It has been obtained in small quantities by some authors (Fourneau and Tideneau, Comptes rendus 141 (1905), 663; V. Paolini, Gazz 42, I (1912), 30 and Atti della R. Accad. dei Lincei (5), 20 (1911), 940; E. mosettig, Ber. 62 (1929), 1274, but none of them mentions the odor.

Pure 2-methyl-3-(3'-4-methylenedioxyphenyl) propanal as an olfactory ingredient, admixture with the indicated additional components in the given amounts:

Example I A perfume oil having a cyclamen character was made by mixing together the following ingredients:

Parts by weight 2-methyl-3-(3',4,-methylenedioxyphenol)-propanal 50 Hydroxyeitronellal 12 Linalool 4 Alpha ionone 5 Linalyl acetate 4 Geraniol ex Java citronella oil 3 Phenyl ethyl alcohol 5 Musk ketone 2 Amyl cinamic aldehyde 5 Benzyl acetate 5 Terpineol t 5 Example II A perfume oil having a jasmin character was mixed from the following ingredients:

Parts by weight 2-methyl-3-(3',4-methylenedioxypheny1)-propanal 50 Amyl cinnamic aldehyde 13 Benzyl acetate 10 Linalool 5 Linalyl acetate 5 Hydroxy citronallal 5 Heliotropin 4 Phenyl ethyl alcohol 8 Example 111 Alpha ionone Geranyl acetate Aldehyde C undecylenic What we claim is l. A composition consisting ofperfume oil and Z-methy1-3- 3 ',4'-methylene dioxyphenyl) -prop anal.

2. A composition consisting of a perfume oil, a fragrance-imparting proportion of 2-methyl-3-(3',4'-methylenedioxyphenyl)-propanal and perfume diluents.

3. A composition consisting of a perfume oil having exceptional tenacity and a sulficient amount of 2-methyl-3- (3 ,4-methylenedioxyphenyl) -propanal to impart the fragrance of the propanal to the oil, and a cosmetic carrier compatible with the propanal.

References Cited by the Examiner UNITED STATES PATENTS 3,008,968 11/61 Beets 1679'4 X OTHER REFERENCES Bogert et al.: J. Am. Chem. Soc., vol. 53, pages 2747-2755 (1931).

Moncrief: The Chem. of Perf. Materials, United Trade Press, London, 1949, pp. 38, 39, 84.

FRANK CACCIAPAGLIA, 111., Primary Examiner.

IRVING MARCUS, LEWIS GOTTS, Examiners. 

1. A COMPOSITION CONSISTING OF PERFUME OIL AND 2-METHYL-3-(3'',4''-METHYLENEDIOXYPHENYL)-PROPANAL. 